Skip to content

Anna Maria Island house rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated house rentals in Anna Maria Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

  1. Entire home
  2. Anna Maria
Cozy Beachhouse 800 steps to beach

This beautiful home is only 800 steps from one of the most beautiful beaches in Southwest Florida. Great getaway for couples. Amazing restaurants and entertainment very close. Free trolley, endless things to do: kayaking, sunbathing, and relaxing.

R2,302 ZAR per night
SUPERHOST
  1. Entire home
  2. Anna Maria
SunKissed Cottage

Beachfront, North End, large 2 bedroom with expansive views of the dolphins frolicking in the azure waters of the North End of Anna Maria Island. BBQ grill, bikes, paddle boards, kayak and a golf cart all included. Your backyard is a beautiful view of Egmont Key & the Skyway Bridge and your front yard is a lushly landscaped private, heated pool. Walk to the Rod & Reel Pier where dolphins frolic every afternoon or walk to Pine Avenue for some local shopping.

R12,039 ZAR per night
SUPERHOST
  1. Entire home
  2. Holmes Beach
The Peachy Beach House, steps to the gulf

Just opened up for June ‘22. Please note- PRICE IS GREATLY DECREASED BECAUSE POOL CONSTRUCTION happening. Heavy construction is complete Steps from semi-private gulf beach, this 3 story on a quiet street in north Holmes Beach has all you need for a wonderful beach vacation. Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new (May 2021) tempurpedic king bed with gulf views. You’ll find: crib, high chair, beach chairs, wagon, umbrella, beach toys and towels!

R3,460 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Villas
  • Hotels

Anna Maria Island vacation rentals

  1. Entire rental unit
  2. Holmes Beach
Villa Shrimp - Cute Studio Villa at Islands West Resort! Vacay in luxury so close to the beach!
R1,937 ZAR per night
  1. Entire rental unit
  2. Holmes Beach
Villa Sand Dollar - New, fun and close to the beach, 1 bedroom Villa at the Islands West Resort!
R2,268 ZAR per night
SUPERHOST
  1. Entire cottage
  2. Anna Maria
Turtle Cottage - Anna Maria Island
R4,162 ZAR per night
SUPERHOST
  1. Entire cottage
  2. Bradenton Beach
Bradenton Beach Sunsets II
R2,936 ZAR per night
  1. Entire rental unit
  2. Holmes Beach
Little Dream by Anna Maria Island Accommodations
R1,260 ZAR per night
  1. Entire bungalow
  2. Anna Maria
Bay Breeze Cottages #2
R4,606 ZAR per night
  1. Entire rental unit
  2. Anna Maria
Low Tide by AMI Locals
R6,473 ZAR per night
  1. Entire rental unit
  2. Holmes Beach
Soakin up Sun by AMI Locals
R1,087 ZAR per night
  1. Entire condo
  2. Holmes Beach
Beachfront Bungalow! Newly updated 1 bedroom!
R4,354 ZAR per night
  1. Entire rental unit
  2. Bradenton Beach
Lovely 1 bedroom apartment with partial water view
R2,920 ZAR per night
SUPERHOST
  1. Entire condo
  2. Holmes Beach
Beach Escape - Make Memories on Anna Maria Island!
R2,637 ZAR per night
  1. Entire rental unit
  2. Holmes Beach
Villa Seashell - Amazing 1 bedroom Villa at new Islands West Resort! Close to beach with pool!
R1,591 ZAR per night

Anna Maria Island villa rentals

  1. Entire villa
  2. Holmes Beach
CALICO★Tropical Pool★Walk to Beach★Family Friendly
R7,877 ZAR per night
SUPERHOST
  1. Entire villa
  2. HOLMES BEACH
Casa Coconut AMI#1 @Manatee Beach
R2,542 ZAR per night
  1. Entire villa
  2. Holmes Beach
Comfortable island villa with private heated pool, courtyard & easy beach access
R3,496 ZAR per night
SUPERHOST
  1. Entire villa
  2. HOLMES BEACH
Manatee Beach 1BR at Casa Coconut AMI#3
R2,207 ZAR per night
  1. Entire villa
  2. Holmes Beach
Newly-built home near Gulf beaches with heated private pool & free WiFi
R5,181 ZAR per night
  1. Entire villa
  2. Holmes Beach
Island villa with heated private pool, tranquil courtyard, easy beach access
R3,449 ZAR per night
  1. Entire villa
  2. Holmes Beach
Upscale tropical getaway with private pool & spa, elevator, and more
R5,811 ZAR per night
  1. Entire villa
  2. Holmes Beach
Chic on the Beach Side B
R5,118 ZAR per night
  1. Entire villa
  2. Holmes Beach
PALM HAVEN BEACH SIDE VILLA
R3,544 ZAR per night
  1. Entire villa
  2. Holmes Beach
Welcoming condo close to the beach with heated private pool and free WiFi
R4,961 ZAR per night
  1. Entire villa
  2. Anna Maria
Northshore Beach House - North Anna Maria Island
R3,481 ZAR per night
  1. Entire villa
  2. Holmes Beach
BEACH WALK #1 BEACH SIDE VILLA
R3,265 ZAR per night

Anna Maria Island condo rentals

SUPERHOST
  1. Entire condo
  2. Holmes Beach
Ocean View Oasis
R1,512 ZAR per night
SUPERHOST
  1. Entire condo
  2. Bradenton Beach
★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
R3,807 ZAR per night
  1. Entire condo
  2. Bradenton Beach
Anna Maria Island Beach Waves
R2,315 ZAR per night
  1. Entire condo
  2. Holmes Beach
Anna Maria by the Bay (minimum rental is 30 days)
R1,811 ZAR per night
  1. Entire condo
  2. Holmes Beach
Coconuts Beachfront #110, amazing just-updated 1 bedroom beachfront condo!
R3,701 ZAR per night
  1. Entire condo
  2. Bradenton Beach
Amazing View, Updated Beachfront Condo
R3,562 ZAR per night
SUPERHOST
  1. Entire condo
  2. Holmes Beach
Beach, Pool, Tennis, Bikes, Close to Everything
R2,110 ZAR per night
  1. Entire condo
  2. Bradenton Beach
Anthony Beach Cottages - Gulf View Condo
R4,331 ZAR per night
  1. Entire condo
  2. Bradenton Beach
Beachfront view, toes in the sand and gulf. Simply paradise, book now your beach chair is waiting!
R3,503 ZAR per night
SUPERHOST
  1. Entire condo
  2. Holmes Beach
Beach Haven #204
R3,150 ZAR per night
SUPERHOST
  1. Entire condo
  2. Bradenton Beach
Beachfront condo in paradise
R3,555 ZAR per night
  1. Entire condo
  2. Holmes Beach
Island Paradise #4 - Stunning Gulf Front Views
R3,276 ZAR per night

Your guide to Anna Maria Island

Introduction

With its beautiful beaches and brilliant blue waters, this seven-mile barrier island offers a nostalgic idyll on the Gulf of Mexico. Over the years, residents have proudly resisted development, so Anna Maria’s vibe is decidedly low-key, with thatched-roof open-air bars and fresh fish restaurants dotting the waterfront. Here, where the island-wide speed limit is 35 miles per hour, the pace of life is literally slower. There are three small towns on the island — Bradenton Beach in the south, Holmes Beach in the middle, and the largest, Anna Maria, in the north — each with its own charms.


How do I get around Anna Maria Island?

Sarasota-Bradenton International Airport (SRQ) is the closest airport at 20 miles away. You can take a taxi or rent a car to carry you over one of the two bridges that connect Anna Maria Island to the mainland. Once you settle in, you may not use a car much. The island is extremely walkable, and operates a free trolley between 6 a.m. and 10 p.m. with 14 stops, including at the beaches. Many visitors also choose to rent bikes or golf carts.


When is the best time to stay in a vacation rental in Anna Maria Island?

January through April and October through December are popular months to visit as they offer temperatures between 70 and 80 degrees Fahrenheit. April and May bring temperatures in the high 80s, and June through September can be quite hot, with temperatures in the 90s. If you opt to book one of the area’s vacation rentals for a winter holiday, make sure to pack a layer for cooler evenings.


What are the top things to do in Anna Maria Island?

Coquina Beach

You won’t have trouble finding a spot for your towel on this serene beach with sand dunes and waving beach grass. Although more sedate than nearby Manatee Public Beach, which draws more crowds, Coquina Beach doesn’t scrimp on amenities. There are picnic tables, bathrooms, and a lifeguard, making it an ideal spot for families. Bring a picnic, or fuel up at the Coquina Beach Cafe, which serves breakfast, fish tacos, and — for the grown-ups — frozen drinks at its tiki bar.

Coquina Baywalk

Get acquainted with the island’s unique ecosystem on this short walk through Leffis Key Preserve on an elevated wooden walkway. You’ll see mangrove trees alongside thousands of native plant species. You’re also likely to spot local wildlife such as geckos, crabs, stingrays, and birds — including the remarkable frigatebird, famous for showboating males who inflate an enormous red pouch under their beaks when courting.

Bean Point Beach

If you’re yearning for that Robinson Crusoe feel, Bean Point Beach is your best bet. Located on the northern tip of the island, this gorgeous stretch of sand is where the island’s founding family, chose to build their estate in 1892. Their homestead is long gone, but the beauty that drew them to the land is very much present. Off the beaten path, this public beach has no parking lots or lifeguard. What it does have is scenic splendor, a calming sense of privacy, and unobstructed sunset views.